Studies of Tertiary Amine Oxides. Part 13. Solvent Effects on the Rate of Thermal Rearrangement of N-(2,4-Dinitrophenyl)piperidine N-Oxide

Article abstract of DOI:10.1039/P29880001157

The rearrangement of N-(2,4-dinitrophenyl)piperidine N-oxide was studied in ten aprotic solvents.Different correlations of the first-order rate coefficients (k_obs.) with several solvent parameters were examined for the ten solvents with a range of 45 units in dielectric constant; the multiparameter equations of Krygowski and Fawcett, Koppel and Palm, and Kamlet and Taft were all examined.The k_obs. values were correlated reasonably well with the Lewis basicity of the solvent, Gutmann's donor number, and Dimroth's E_T(30) parameter when hydrogen-bond-donor solvents were excluded.